Potassium Carbonate → 2,6-Dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(3-[4-(2-tetrahydropyran-2-yloxyethyl)phenoxy]propoxycarbonyl)-1,4-dihydropyridine

HRID 34416Notes

Reaction equation

HRID 34416 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.[CH3:17][C:18]1[NH:19][C:20]([CH3:44])=[C:21]([C:37]([O:39][CH2:40][CH2:41][CH2:42]Br)=[O:38])[CH:22]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([N+:34]([O-:36])=[O:35])[CH:29]=2)[C:23]=1[C:24]([O:26][CH3:27])=[O:25].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:17][C:18]1[NH:19][C:20]([CH3:44])=[C:21]([C:37]([O:39][CH2:40][CH2:41][CH2:42][O:16][C:13]2[CH:12]=[CH:11][C:10]([CH2:9][CH2:8][O:7][CH:2]3[CH2:3][CH2:4][CH2:5][CH2:6][O:1]3)=[CH:15][CH:14]=2)=[O:38])[CH:22]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([N+:34]([O-:36])=[O:35])[CH:29]=2)[C:23]=1[C:24]([O:26][CH3:27])=[O:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 32742783-bromopropyl Methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylateHCID 142087834-(2-Tetrahydropyran-2-yloxyethyl)phenol

Product 1

HCID 142087862,6-Dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(3-[4-(2-tetrahydropyran-2-yloxyethyl)phenoxy]propoxycarbonyl)-1,4-dihydropyridine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-(2-Tetrahydropyran-2-yloxyethyl)phenol (9, 72.1 g, 0.32 mol) was added to a solution of 2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(3-bromopropoxycarbonyl)-1,4-dihydropyridine (12, 105 g, 0.23 mol) and K2CO3 (48 g, 0.35 mol) in acetone (700 mL), and the mixture heated at reflux overnight. After cooling, the solid was filtered, the solvent removed under reduced pressure, and the residue solubilised in CH2Cl2 (1 L). The organic layer was washed with 10% NaOH (2×100 mL) and water (2×100 mL) and dried over sodium sulfate. The solvent was evaporated under reduced pressure to provide an oil which was purified by flash chromatography (EtOAc: CH2Cl2 --15:85) to yield 2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(3-[4-(2-tetrahydropyran-2-yloxyethyl)phenoxy]propoxycarbonyl)-1,4-dihydropyridine (1, mp<50° C.).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux overnight
  3. temperatureAfter cooling
  4. filtrationthe solid was filtered
  5. customthe solvent removed under reduced pressure
  6. washThe organic layer was washed with 10% NaOH (2×100 mL) and water (2×100 mL)
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customto provide an oil which
  10. customwas purified by flash chromatography (EtOAc: CH2Cl2 --15:85)

Sources & evidence

ORD record
ord-342840a0d7e147bd89b349781f9f0701
Source dataset
uspto-grants-1988_08
Patent number
US04761420

Reaction notes

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